I'd point out that there is a difference between a boat that can be transported on a trailer and a truly trailerable boat, which does not require anything but a proper boat ramp to launch the boat. Many of the boats mentioned above are boats that can be trailered, but not truly trailerable boats.
The Corsair 36 trimaran is a good bluewater capable trailerable... expensive and big... but doesn't require anything more than a boat ramp to launch it.
I'd also point out that you do not need a bluewater boat to make the hop from Florida to the Bahamas, as many coastal cruisers do that on a regular basis. You do need to have the patience to wait for the right weather window though.
Finally, one of my boat's sister-ships started in Florida, went down into the Caribbean, first east, a bit south and then west...then crossed to Honduras and is currently in Rio Dulce, Guatemala. This was a 3500 NM trip in a trailerable sport trimaran. So it is doable in a small boat.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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